Methanol → HCID 57962578, compound

HRID 541890Notes

Reaction equation

HRID 541890 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:11][CH2:10]2)=[O:8])[CH:3]=1.CO.[OH-].[Na+]>O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]2)=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57962295Methyl 1-[(5-methyl-3-isoxazolyl)carbonyl]-4-piperidineacetate

Product 1

HCID 57962578HCID 57962578, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into the reaction flask was added methyl {1-[(5-methylisoxazol-3-yl)carbonyl]piperidin-4-yl}acetate (2.8 g, 10.0 mmol) and methanol (10 mL) and 3 M of sodium hydroxide in water (10 mL). The mixture was stirred at rt for 2 h. After concentration, the residue was neutralized to pH=7. The mixture was extracted with EtOAc twice. The combined organic layers were dried and concentrated to give the desired product (0.30 g, 11%). LCMS for C12H17N2O4 (M+H)+: m/z=253.1

Workup

  1. concentrationAfter concentration
  2. extractionThe mixture was extracted with EtOAc twice
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9486cfc16134d89ae597445da8b80fe
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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